I have a 16,000 plus digital audio collection and I use Media Monkey to manage my files. One feature of Media Monkey is you can sort your collection based on the number of times played. This playlist is based on the top music and/or music video files I played/listened/streamed from my server in 2019.
The list is in no particular order and starts with Dread Mar-I. Dread Mar-I is a Argentine reggae singer, songwriter, and bandleader.